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I bought a babydoll dress and a thong white mesh with little hearts printed all over it. I was in uniform I said it was for my girlfriend, but the sales ladie knew my girlfriend was the same size as me.

Most of my early stuff came from girlfriends. The first thing I bought myself was a pair of 4.5" single sole, black stilettos. They are a classic pump, slightly pointy toe but not too much. I still have them, I still have trouble walking in them. 4" is about my limit for walking naturally, any higher than that and I get that can't straighten the knee fully silly girl walk. Regardless, they're sexy shoes and I love wearing them.

I bought a babydoll dress and a thong white mesh with little hearts printed all over it. I was in uniform I said it was for my girlfriend, but the sales ladie knew my girlfriend was the same size as me.

You know I think they see straight through the pretence a lot of the time.

My first female clothing purchase was two 4-packs of string bikini panties, and later that same week a steel boned under-bust corset, which I took back the very next day and exchanged for a full corset, because the under-bust one gave me way to much 'muffin top'. I didn't have to talk to anyone about the panties, but actually admitted to the SA at the corset shop that the corset was for me, even though I was fully en-drab.

In a very deep closet but I'm opening the door a little to see a new world

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The first items I brought myself was some white lacy stockings and suspender belt with a pink silk night slip dress. I spent most evenings when I was single wearing these, they made me feel very girly and pretty. xxx

yup It was after that I decided to quit pretending in a place like L.A. or Tel Aviv it's very easy to just go and buy what you like in Drab or Femme. Where I live now oh boy, had an interesting time at sally's hair supply yesterday

Well, if pantyhose count as clothing that was my first purchase.
But the first true article would have to be the black patent
5" stiletto pointed toe pumps I ordered from Fredericks of Hollywood.
Had them for about 21 years before they fell apart. Of course they were
never worn outside but had many indoor miles on them.

I bought while in high school one of those Golden Playtex Magic Controllers that were made of rubber or latex from Marshall Fields. I purged and then I think I bought a second one which I also purged. I came home from college and bought a floor length nylon peignoir which I wore at nights and kept hidden in a drawer. I wore it in from of my future wife who approved and the rest is history.

The very first item was a pair of nylon pantyhose that my Gunnery Sgt recommended all of us in our unit (about six of us) wear on our a 15 mile hike the battalion was scheduled to do. He said it would help compress our legs and help with circulation and help prevent blisters.

I don't recall it doing either of those two things. In fact, I think the nylon made my feet itch and gave me a blister.
Maybe he was hazing us. :|

The very first thing for me as far as I could remember was a pair of pantyhose from a corner store. The funny part was, not being asked by the Chinese worker but felt like I had to explain I told him I was painting and had to use the pantyhose to strain the paint, he was so nice that he told me to wait and then handed me a bag with about ten pairs of pantyhose telling me that they were from packages that ladies open and don't buy them or from packages that came damaged and he can't sell. I thanked him and had pantyhose for a while. I think about it now and laugh.

I think the first item might have been a amazing pink pushup bra and thong from VS. Unfortunately, the Thong didn't fit at all and soon lost the bra in a mini-purge. After a couple sizing wrong puchases the ones I will remember are the 5 platforms I bought on ebay that fit perfect. They are amazing but super impractical and then a few week later I nailed my size on my first purchase of skinny jeans at Target. I was so happy they fit and felt great.

The crossdressing community is one that needs to stick together and continue to be there for each other for whatever one needs. We are always trying to improve the forum to better serve the crossdresser in all of us.